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What Is

Career Like A BOSS?

Welcome to Career Like A BOSS, where accelerating your team’s careers and meaningful advancement is our goal. We are transforming professional growth through expert-led courses and a vibrant community. Drawing from our founder’s climb from modest beginnings to leadership in the boardroom, we offer insights for every career stage.

The Driving Force Behind Career Like A BOSS

From humble beginnings to a stellar career navigating the upper echelons of tech giants, Craig Stilwell's journey is a testament to relentless pursuit and visionary leadership.


His experience spans over three decades, marked by rapid promotions and strategic growth leading to C-Level officer roles, as well as Senior and Executive VP roles at multi-billion dollar tech companies like Citrix, OpenText and Carbonite as well as early leadership roles at Accenture.


Craig's passion now lies in sharing this wealth of knowledge and experience alongside his network of high achievers and industry executives, aiming to empower professionals across the globe to seize their careers with confidence. Beyond his professional achievements, Craig's approachable persona and dedication to mentoring encapsulates the spirit of Career Like A BOSS—where every professional is seen, supported, and inspired to excel.

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Crafting Millions of Leaders: The Vision

At Career Like A BOSS, we deeply believe that every professional deserves access to the tools, knowledge, and community support needed to thrive in their careers.

Our mission is to help millions of professionals advance and accelerate their careers through our courses and community of like-minded professionals. We're committed to helping you navigate the complexities of the professional world, ensuring you're equipped to make informed decisions, embrace leadership opportunities, and, ultimately, own your career trajectory with confidence and clarity.

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Unlock Your Potential

  • Want to accelerate your career?

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    Our courses are meticulously designed to unlock your potential at any career stage, offering strategies for advancement from industry giants. Whether you are an entry-level employee or a seasoned executive, you'll find personalized paths to escalate your career trajectory and achieve your professional goals.

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  • Want mentoring from C-level industry leaders?

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    Dive into a wealth of knowledge with our exclusive content from global industry leaders. From the former CEO of Citrix Systems to VP of IBM, get unparalleled insights and advice that's usually inaccessible. This direct exposure to thought leadership can inspire innovation and provide a competitive edge in your professional journey.

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  • Want to elevate your leadership profile?

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    Elevate your leadership skills through courses focused on critical thinking, decision-making, and strategic planning. Our content is not just theoretical; it includes practical tips, real-world applications, and actionable advice that you can immediately apply to your work life, enhancing your effectiveness as a leader and a visionary in your field.

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  • Want advice from like-minded professionals?

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    Engage with our vibrant, ever-growing community of professionals who are just as driven and ambitious as you. This network not only provides moral support but also opens up opportunities for collaboration, networking, and mentorship. It's a space to share challenges, solutions, and success stories, making your professional journey less isolating and more empowered.

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Elevate Your Career with Us

Accelerate Your Career Growth

Networking Opportunities

Achievement Focus

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